100 Fun Questions to ask Friends

Looking for fun questions to ask friends? Whether you’re on the phone and need something to talk about, sitting around the dinner table trying to keep the conversation going, or just hanging out and wanting to learn something new about each other, I’ve got you covered with this massive list of questions to ask your friends.

Some of these questions are completely random and funny, while others are a little more thoughtful and deep. So grab your friends, pick a few questions, and see where the conversation takes you.

Fun Questions to ask Friends

1. If you could plan your perfect day from beginning to end, what would you do?

2. What is something you could talk about for hours without getting bored?

3. If someone gave you a free plane ticket right now, where would you go?

4. What is your current favorite thing to do when you have absolutely no plans?

5. If you could instantly become really good at one hobby, what would you choose?

6. What is one food you could probably eat every week and never get tired of?

7. What song immediately puts you in a good mood?

8. If your life had a theme song right now, what would it be?

9. What is something small that always makes your day better?

10. If you could live inside any TV show for a week, which one would you choose?

11. What is your dream vacation?

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12. If you could make one fictional place real, which one would you choose?

13. What would your dream house definitely have inside?

14. If you could switch lives with someone for 24 hours, who would it be?

15. Which app would be the hardest for you to delete permanently?

16. If you had an unlimited shopping budget at one store, which store would you choose?

17. What is one thing you think everyone should experience at least once?

18. If you could relive one day from the past year, which day would you choose?

19. What is something you are currently looking forward to?

20. What is your perfect Saturday?

21. What is one activity you have always wanted to try?

22. If you could wake up tomorrow anywhere in the world, where would you want to be?

23. What is one place you think we absolutely need to travel to together?

24. What is one thing you would buy immediately if money were not an issue?

25. What is something you think you will still love when you are 80?

26. If you could rename yourself, what name would you choose?

27. Which holiday would you add to the calendar if you could create your own?

28. If you could only eat breakfast, lunch, or dinner foods for the rest of your life, which would you choose?

29. If you had to open a restaurant tomorrow, what would you serve?

30. What color best describes your personality?

Fun Questions to ask With Friends 

31. If your bedroom had to be decorated around one completely random theme, what would you choose?

32. Which celebrity would you trust to plan your birthday party?

33. What would you name a boat if you owned one?

34. If you had to teach a class about something that has nothing to do with your career, what would you teach?

35. What would your perfect coffee shop look like?

36. If you could bring back one fashion trend, which one would you choose?

37. What is the most embarrassing thing you believed as a kid?

38. What is your most irrational fear?

39. If your search history was accidentally shown on a giant screen, how nervous would you be?

40. What is the weirdest food combination you actually enjoy?

41. If you were arrested and nobody knew why, what would your friends assume you did?

42. What is the funniest excuse you have ever used to get out of something?

43. Which animal do you think would have the most attitude if it could talk?

44. What is something completely normal that you are weirdly bad at?

45. If your life were a reality show, what would it be called?

46. What is your most useless talent?

47. What is something you would be absolutely terrible at doing professionally?

48. Which fictional character would annoy you the most in real life?

49. What is the funniest thing you have ever done because you were embarrassed?

50. If you had to wear one Halloween costume every day for an entire year, what would you choose?

Questions to ask Your Friends

51. What is your funniest childhood memory?

52. If you suddenly became famous tomorrow, what do you think it would be for?

53. What is one trend you participated in that you wish nobody had pictures of?

54. What is the pettiest thing that annoys you?

55. If your pet could expose one secret about you, what would it be?

56. What is something you refuse to do even though everyone says it is easy?

57. When did you realize we were actually becoming close friends?

58. What is something you are really proud of yourself for?

59. What is the funniest argument or disagreement we have ever had?

60. Where do you think we will both be 10 years from now?

61. What season of your life has changed you the most?

62. What is something you are still figuring out about yourself?

63. What is something you think we will still be doing together when we are older?

64. When do you feel the most like yourself?

65. What is something you wish your younger self knew?

66. What is one lesson you had to learn the hard way?

67. Who has had the biggest influence on the person you are today?

68. What does a successful life look like to you?

69. What is something you used to care about that does not matter to you anymore?

70. What do you want more of in your life right now?

71. What is something you have recently changed your mind about?

72. What makes you feel the most supported?

73. What is something you are scared to do but really want to try?

74. What is one part of your personality that you have learned to appreciate more?

75. What is something you want to accomplish within the next few years?

76. What does friendship mean to you now compared to a few years ago?

77. When do you feel the most confident?

78. What is a boundary you have gotten better at setting?

79. What kind of person do you hope to become?

80. What is something you hope never changes about your life?

Fun Questions to ask a Friend

81. What do you think makes our friendship work?

82. What is one thing you know you can always come to me about?

83. If you had to describe our friendship in three words, what would they be?

84. What’s the best life advice you’ve ever heard?

85. What is something you want to get better at this year?

86. If you could repeat one age of your life for a year, what age would you choose?

87. What is one memory that always makes you smile?

88. What is something you wish you made more time for?

89. If you could have dinner with anyone from history, who would you choose?

90. What is one thing that can instantly make a bad day better?

91. If you could try any career for one week, what would you choose?

92. What is something you think you would regret not doing at least once?

93. What is one compliment you have received that you still remember?

94. What is something you think people misunderstand about you?

95. If you could see one moment from your future, what would you want to see?

96. What is one tradition you would love to start with your friends?

97. What is something you have always wanted to learn how to do?

98. If you could have one year completely free from responsibilities, how would you spend it?

99. What is one thing you hope we get to experience together someday?

100. If we opened a time capsule 10 years from now, what would you put inside it today?